Acetylene derivatives and crop protection agents containing them
Acetylene derivatives of the general formula I ##STR1## where U, V and W are hydrogen, halogen, nitro, cyano, alkyl or alkoxy,A is alkylidene, alkoxymethylidene, alkylthiomethylidene or alkoximino,B is OH, alkoxy or alkylamino andR is hydrogen, halogen, cyano, CF.sub.3, alkyl, cycloalkyl, haloalkyl, aryl, alkenyl, alkynyl, heterocyclyl, hetaryl, arylalkyl, arylalkenyl, arylethynyl, hetaryl-C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -alkoxy-C.sub.1 -C.sub.4 -alkyl, aryloxyalkyl, hetaryloxyalkyl, arylamino-alkyl, arylthiomethyl, hetarylthiomethyl, C(O)R.sup.1, C(O)NR.sup.2 R.sup.3, C(S)NR.sup.4 R.sup.5, C(O)SR.sup.6, C(S)OR.sup.7, C(S)SR.sup.8, CH(OH)R.sup.9, CH(OR.sup.10)R.sup.11, SiR.sup.12 R.sup.13 R.sup.14, SnR.sup.15 R.sup.16 R.sup.17, C(OR)R.sup.18 or C(.dbd.N--OR.sup.19)R.sup.20 andR.sup.1 -R.sup.17, R.sup.19 and R.sup.20 are hydrogen, alkyl, aryl, hetaryl, arylalkyl or hetarylalkyl and R.sup.18 is OH, C.sub.1 -C.sub.4 -alkoxy or aryl-C.sub.1 -C.sub.4 -alkoxy, and fungicides containing these compounds.
Latest BASF Aktiengesellschaft Patents:
- Wheat plants having increased tolerance to imidazolinone herbicides
- Method for the classification of water absorbent polymer particles
- Method of forming a composite component
- HERBICIDE-RESISTANT SUNFLOWER PLANTS, POLYNUCLEOTIDES ENCODING HERBICIDE-RESISTANT ACETOHYDROXYACID SYNTHASE LARGE SUBUNIT PROTEINS, AND METHODS OF USE
- HERBICIDE-RESISTANT SUNFLOWER PLANTS, POLYNUCLEOTIDES ENCODING HERBICIDE-RESISTANT ACETOHYDROXYACID SYNTHASE LARGE SUBUNIT PROTEINS, AND METHODS OF USE
Claims
1. An acetylene derivative of the formula I ##STR32## where U, V and W are identical or different and are each hydrogen, halogen, nitro, cyano, C.sub.1 -C.sub.4 -alkyl or C.sub.1 -C.sub.4 -alkoxy,
- A is C.sub.1 -C.sub.4 -alkylidene, C.sub.1 -C.sub.4 -alkoxymethylidene, C.sub.1 -C.sub.4 -alkylthiomethylidene or C.sub.1 -C.sub.4 -alkoximino,
- B is OH, C.sub.1 -C.sub.4 -alkoxy or C.sub.1 -C.sub.4 -alkylamino and
- R is unsubstituted or substituted hetaryl selected from the group consisting of pyridyl, 2-pyridyl, 3-pyridyl, 4-pyridyl, pyrimidinyl, 4-pyrimidinyl, 2-pyrimidinyl, thienyl, 2-thienyl, 3-thienyl, furyl, 2-furyl, 3-furyl, 1-pyrrolyl, 5-isoxazolyl, 3-isoxazolyl, 1,3,4-oxadiazol-2-yl, 1,2,4-oxadiazol-5-yl, 1,3,4-thiadiazol-2-yl, 1-imidazolyl, 1,2,4-triazolyl, 1,3,4-triazolyl, 4-thiazolyl and 2-benzothiazolyl,
- the term "unsubstituted or substituted" denoting, in addition to hydrogen, halogen, cyano, nitro, C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -alkoxy, C.sub.1 -C.sub.4 -haloalkyl, C.sub.1 -C.sub.4 -haloalkoxy, C.sub.1 -C.sub.4 -alkoximino-C.sub.1 -C.sub.4 -alkyl, aryl, aryloxy, benzyl, benzyloxy, hetaryl, hetaryloxy, C.sub.3 -C.sub.6 -cycloalkyl, C.sub.1 -C.sub.4 -dialkylamino, CO.sub.2 Me, CO.sub.2 Et, formyl or acyl, Me is methyl and Et is ethyl, and the term "hetaryl" denoting an aromatic five-membered or six-membered heterocyclic structure.
2. An acetylene derivative of the formula II ##STR33## where R is as defined in claim 1.
3. An acetylene derivative of the formula IV ##STR34## where R is as defined in claim 1.
4. An acetylene derivative of the formula V ##STR35## where R is as defined in claim 1.
5. An acetylene derivative of the formula VI ##STR36## where R is as defined in claim 1.
6. A fungicide containing an inert carrier and a fungicidally effective amount of an acetylene derivative of the formula I ##STR37## where U, V and W are identical or different and are each hydrogen, halogen, nitro, cyano, C.sub.1 -C.sub.4 -alkyl or C.sub.1 -C.sub.4 -alkoxy,
- A is C.sub.1 -C.sub.4 -alkylidene, C.sub.1 -C.sub.4 -alkoxymethylidene, C.sub.1 -C.sub.4 -alkylthiomethylidene or C.sub.1 -C.sub.4 -alkoximino,
- B is OH, C.sub.1 -C.sub.4 -alkoxy or C.sub.1 -C.sub.4 -alkylamino and
- R is unsubstituted or substituted hetaryl selected from the group consisting of pyridyl, 2-pyridyl, 3-pyridyl, 4-pyridyl, pyrimidinyl, 4-pyrimidinyl, 2-pyrimidinyl, thienyl, 2-thienyl, 3-thienyl, furyl, 2-furyl, 3furyl, 1-pyrrolyl, 5-isoxazolyl, 3-isoxazolyl, 1,3,4-oxadiazol-2-yl, 1,2,4-oxadiazol -5-yl, 1,3,4-thiadiazol-2-yl, 1-imidazolyl, 1,2,4-triazolyl, 1,3,4-triazolyl, 4-thiazolyl and 2-benzothiazolyl,
- the term "unsubstituted or substituted" denoting, in addition to hydrogen, halogen, cyano, nitro, C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -alkoxy, C.sub.1 -C.sub.4 -haloalkyl, C.sub.1 -C.sub.4 -haloalkoxy, C.sub.1 -C.sub.4 -alkoximino-C.sub.1 -C.sub.4 -alkyl, aryl, aryloxy, benzyl, benzyloxy, hetaryl, hetaryloxy, C.sub.3 -C.sub.6 -cycloalkyl, C.sub.1 -C.sub.4 -dialkylamino, CO.sub.2 Me, CO.sub.2 Et, formyl or acyl, Me is methyl and Et is ethyl, and the term "hetaryl" denoting an aromatic five-membered or six-membered heterocyclic structure.
7. A method of combating fungi, wherein the fungi, or the materials, plants or seeds to be protected against fungus attack, or the soil are treated with a fungicidally effective amount of a compound of the formula ##STR38## where U, V and W are identical or different and are each hydrogen, halogen, nitro, cyano, C.sub.1 -C.sub.4 -alkyl or C.sub.1 -C.sub.4 -alkoxy,
- A is C.sub.1 -C.sub.4 -alkylidene, C.sub.1 -C.sub.4 -alkoxymethylidene, C.sub.1 -C.sub.4 -alkylthiomethylidene or C.sub.1 -C.sub.4 -alkoximino,
- B is OH, C.sub.1 -C.sub.4 -alkoxy or C.sub.1 -C.sub.4 -alkylamino and
- R is unsubstituted or substituted hetaryl selected from the group consisting of pyridyl, 2-pyridyl, 3-pyridyl, 4-pyridyl, pyrimidinyl, 4-pyrimidinyl, 2-pyrimidinyl, thienyl, 2-thienyl, 3-thienyl, furyl, 2-furyl, 3-furyl, 1-pyrrolyl, 5-isoxazolyl, 3-isoxazolyl, 1,3,4-oxadiazol-2-yl, 1,2,4-oxadiazol-5-yl, 1,3,4-thiadiazol-2-yl, 1-imidazolyl, 1,2,4-triazolyl, 1,3,4-triazolyl, 4-thiazolyl and 2-benzothiazolyl,
- the term "unsubstituted or substituted" denoting, in addition to hydrogen, halogen, cyano, nitro, C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -alkoxy, C.sub.1 -C.sub.4 -haloalkyl, C.sub.1 -C.sub.4 -haloalkoxy, C.sub.1 -C.sub.4 -alkoximino-C.sub.1 -C.sub.4 -alkyl, aryl, aryloxy, benzyl, benzyloxy, hetaryl, hetaryloxy, C.sub.3 -C.sub.6 -cycloalkyl, C.sub.1 -C.sub.4 -dialkylamino, CO.sub.2 Me, CO.sub.2 Et, formyl or acyl, Me is methyl and Et is ethyl, and the term "hetaryl" denoting an aromatic five-membered or six-membered heterocyclic structure.
8. A method of combating insects, nematodes and mites, wherein the insects, nematodes or mites, or the place where they are located, are treated with an effective amount of a compound of the formula I ##STR39## where U, V and W are identical or different and are each hydrogen, halogen, nitro, cyano, C.sub.1 -C.sub.4 -alkyl or C.sub.1 -C.sub.4 -alkoxy,
- A is C.sub.1 -C.sub.4 -alkylidene, C.sub.1 -C.sub.4 -alkoxymethylidene, C.sub.1 -C.sub.4 -alkylthiomethylidene or C.sub.1 -C.sub.4 -alkoximino,
- B is OH, C.sub.1 -C.sub.4 -alkoxy or C.sub.1 -C.sub.4 -alkylamino and
- R is unsubstituted or substituted hetaryl selected from the group consisting of pyridyl, 2-pyridyl, 3-pyridyl, 4-pyridyl, pyrimidinyl, 4-pyrimidinyl, 2-pyrimidinyl, thienyl, 2-thienyl, 3-thienyl, furyl, 2-furyl, 3-furyl, 1-pyrrolyl, 5-isoxazolyl, 3-isoxazolyl, 1,3,4-oxadiazol-2-yl, 1,2,4-oxadiazol-5-yl, 1,3,4-thiadiazol-2-yl, 1-imidazolyl, 1,2,4-triazolyl, 1,3,4-triazolyl, 4-thiazolyl and 2-benzothiazolyl,
- the term "unsubstituted or substituted" denoting, in addition to hydrogen, halogen, cyano, nitro, C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -alkoxy, C.sub.1 -C.sub.4 -haloalkyl, C.sub.1 -C.sub.4 -haloalkoxy, C.sub.1 -C.sub.4 -alkoximino-C.sub.1 -C.sub.4 -alkyl, aryl, aryloxy, benzyl, benzyloxy, hetaryl, hetaryloxy, C.sub.3 -C.sub.6 -cycloalkyl, C.sub.1 -C.sub.4 -dialkylamino, CO.sub.2 Me, CO.sub.2 Et, formyl or acyl, Me is methyl and Et is ethyl, and the term "hetaryl" denoting an aromatic five-membered or six-membered heterocyclic structure.
9. The acetylene derivative of claim 1, wherein A is C.sub.1 -C.sub.4 -alkylidene.
10. The acetylene derivative of claim 1, wherein A is C.sub.1 -C.sub.4 -alkoxymethylidene.
11. The acetylene derivative of claim 1, wherein A is C.sub.1 -C.sub.4 -alkylthiomethylidene.
12. The acetylene derivative of claim 1, wherein A is C.sub.1 -C.sub.4 -alkoximino.
13. An acetylene derivative of the formula I ##STR40## where U, V and W are identical or different and are each hydrogen, halogen, nitro, cyano, C.sub.1 -C.sub.4 -alkyl or C.sub.1 -C.sub.4 -alkoxy,
- A is C.sub.1 -C.sub.4 -alkylidene, C.sub.1 -C.sub.4 -alkoxymethylidene, C.sub.1 -C.sub.4 -alkylthiomethylidene or C.sub.1 -C.sub.4 -alkoximino,
- B is OH, C.sub.1 -C.sub.4 -alkoxy or C.sub.1 -C.sub.4 -alkylamino and
- R is unsubstituted or substituted hetaryl selected from the group consisting of pyridyl, 2-pyridyl, 3-pyridyl, 4-pyridyl, pyrimidinyl, 4-pyrimidinyl, 2-pyrimidinyl, thienyl, 2-thienyl, 3-thienyl, furyl, 2-furyl, 3-furyl, 1-pyrrolyl, 5-isoxazolyl, 3-isoxazolyl, 1,3,4-oxadiazol-2-yl, 1,2,4-oxadiazol-5-yl, 1,3,4-thiadiazol-2-yl, 1-imidazolyl, 1,2,4-triazolyl, 1,3,4-triazolyl, 4-thiazolyl and 2-benzothiazolyl,
- the term "unsubstituted or substituted" denoting, in addition to hydrogen, halogen, cyano, nitro, C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -alkoxy, C.sub.1 -C.sub.4 -haloalkyl, C.sub.1 -C.sub.4 -haloalkoxy, C.sub.1 -C.sub.4 -alkoximino-C.sub.1 -C.sub.4 -alkyl, aryl, aryloxy, benzyl, benzyloxy, hetaryl, hetaryloxy, C.sub.3 -C.sub.6 -cycloalkyl, C.sub.1 -C.sub.4 -dialkylamino, CO.sub.2 Me, CO.sub.2 Et, formyl or acyl, Me is methyl and Et is ethyl, and the term "hetaryl" denoting an aromatic five-membered or six-membered heterocyclic structure.
14. A method of combatting fungi, wherein the fungi, or the materials, plants or seeds to be protected against fungus attack, or the soil are treated with a fungicidally effective amount of the compound of claim 13.
15. A method of combatting insects, nematodes and mites, wherein the insects, nematodes or mites, or the place where they are located, are treated with an effective amount of the compound of claim 13.
16. The acetylene derivative of claim 1, wherein A is C.sub.1 -C.sub.4 -alkoximino and R is unsubstituted or substituted hetaryl selected from the group consisting of pyridyl, 2-pyridyl, 3-pyridyl, 4-pyridyl, pyrimidinyl, 4-pyrimidinyl, 2-pyrimidinyl, thienyl, 2-thienyl, 3-thienyl, furyl, 2-furyl, 3-furyl, 1-pyrrolyl, 5-isoxazolyl, 3-isoxazolyl, 1,3,4-oxadiazol-2-yl, 1,2,4-oxadiazol-5-yl, 1,3,4-thiadiazol-2-yl, 1-imidazolyl, 1,2,4-triazolyl, 1,3,4-triazolyl, 4-thiazolyl and 2-benzothiazolyl.
17. The acetylene derivative of claim 16, which is methyl 2-(4-(2-chloro)thienylethynyl)phenylglyoxylate O-methyloxime.
18. The acetylene derivative of claim 1, wherein A is NOCH.sub.3 and B is OCH.sub.3.
| 4879085 | November 7, 1989 | Wingert et al. |
| 4937372 | June 26, 1990 | Wenderoth et al. |
| 5449809 | September 12, 1995 | Wingert et al. |
| 0 178 826 | April 1986 | EPX |
| 0244077 | November 1987 | EPX |
| 0 253 213 | January 1988 | EPX |
| 0 260 794 | March 1988 | EPX |
| 0 280 185 | March 1988 | EPX |
| 0 469 411 | February 1992 | EPX |
| 0 477 631 | April 1992 | EPX |
| 2172595 | September 1986 | GBX |
- A(105): 78670 Bushell et al., EP 178876 AZ, 1986 Abstract only.
Type: Grant
Filed: May 18, 1995
Date of Patent: Nov 11, 1997
Assignee: BASF Aktiengesellschaft (Ludwigshafen)
Inventors: Horst Wingert (Mannheim), Beate Hellendahl (Schifferstadt), Reinhard Kirstgen (Neustadt), Hubert Sauter (Mannheim), Eberhard Ammermann (Heppenheim), Gisela Lorenz (Neustadt)
Primary Examiner: Samuel Barts
Law Firm: Oblon, Spivak, McClelland, Maier & Neustadt, P.C.
Application Number: 8/443,460
International Classification: A01N 4382;
